Well, if you are specifically asking about the Droid 2, I don't think it would be worth the money unless you are completely unhappy with the Droid's keyboard and have money to spend. I will say that the Droid seems to have a somewhat special place in Verizon's heart, with it being their first Android phone and all. I wouldn't be surprised if Verizon pushed out gingerbread onto the Droid as well. However, don't be incredibly surprised if they don't, as the phone has already been updated from 2.0.1 to 2.1 and 2.2. I honestly can't think of a phone that has already received two major os updates besides the droid.
Regarding software updates, one of the heads of Android development mentioned about 6 months or so ago that the update process for Android would be slowing down to a more yearly release cycle. However, we have seen the release of Android 2.2 and the imment release of 2.3 in the last few months, so it is hard to take that comment as truth. Especially when Honeycomb is rumored for a release in early 2011.
It is a pain that new hardware and software are getting pushed out at what seems a breakneck pace. However, try and look at the hardware side of the problem from this angle: you have over 6 major (and many more less prominent) technology manufacturers vying for attention in the Android market. It almost seems like the auto industry in some respects.
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